Sugarloaf Key Waterfront Vacation Rentals(28)
Sugarloaf Open Water Home With Beach, Dock and Swimming Canal
- 4 Bedrooms,
- 4 Bathrooms, Sleeps 8
$8,000 -
$10,000
per month
28 night Minimum Stay
- 4 BR,
- 4 BA,
- Sleeps 8
Unparalleled surroundings and 180 degree ocean views.
- 3 Bedrooms,
- 2 Bathrooms, Sleeps 6
$11,200
per month
28 night Minimum Stay
- 3 BR,
- 2 BA,
- Sleeps 6
Incredible, peaceful, Florida Keys getaway home with an exclusive private beach!
- 2 Bedrooms,
- 2 Bathrooms,
- 1 Half Bath, Sleeps 6
- 2 BR,
- 2 BA,
- 1 HF BA,
- Sleeps 6
Exclusive, Private Neighborhood in Lower Sugarloaf
- 3 Bedrooms,
- 2 Bathrooms, Sleeps 6
$6,000
per month
30 night Minimum Stay
- 3 BR,
- 2 BA,
- Sleeps 6
Canalfront Home On A Quiet Street, Only Minutes From Key West.
- 3 Bedrooms,
- 3 Bathrooms, Sleeps 10
$1,505
per week
7 night Minimum Stay
- 3 BR,
- 3 BA,
- Sleeps 10
Spacious Luxury Home with Pool
- 5 Bedrooms,
- 5 Bathrooms, Sleeps 10
$6,200
per month
31 night Minimum Stay
- 5 BR,
- 5 BA,
- Sleeps 10
Open Water Home with Pool, Boat Lift and Tiki Hut
- 3 Bedrooms,
- 2 Bathrooms, Sleeps 8
$2,625
per week
7 night Minimum Stay
- 3 BR,
- 2 BA,
- Sleeps 8
Bayside Beauty in Sugarloaf Key
- 3 Bedrooms,
- 2 Bathrooms, Sleeps 8
- 3 BR,
- 2 BA,
- Sleeps 8
Spectacular Waterfront Paradise
- 3 Bedrooms,
- 3 Bathrooms, Sleeps 12
$7,500
per month
28 night Minimum Stay
- 3 BR,
- 3 BA,
- Sleeps 12
NO LONGER AVAILABLE / SPECTACULAR, HUGE OPEN WATER HOME WITH AMAZING VIEWS!!!
- 3 Bedrooms,
- 2 Bathrooms,
- 1 Half Bath, Sleeps 8
- 3 BR,
- 2 BA,
- 1 HF BA,
- Sleeps 8
Beautiful Open Water Home with Heated Pool and Hot Tub
- 5 Bedrooms,
- 2 Bathrooms, Sleeps 10
$3,200
per week
7 night Minimum Stay
- 5 BR,
- 2 BA,
- Sleeps 10
Ballyhoo Shores - Open Water Oasis
- 3 Bedrooms,
- 2 Bathrooms, Sleeps 6
- 3 BR,
- 2 BA,
- Sleeps 6
Upscale and Spacious Waterfront Property
- 2 Bedrooms,
- 3 Bathrooms, Sleeps 6
- 2 BR,
- 3 BA,
- Sleeps 6
Open Water Luxury 3/3 Pool
- 3 Bedrooms, Sleeps 10
- 3 BR,
- Sleeps 10
VINTAGE SUGARLOAF SHORES HOME ON OPEN WATER CORNER LOT
- 3 Bedrooms,
- 2 Bathrooms, Sleeps 8
$4,900
per month
28 night Minimum Stay
- 3 BR,
- 2 BA,
- Sleeps 8
Stunning Sunsets over Crystal Clear Water in a family friendly setting
- 2 Bedrooms, Sleeps 8
- 2 BR,
- Sleeps 8
Open Water With Pool!
- 5 Bedrooms,
- 3 Bathrooms, Sleeps 10
- 5 BR,
- 3 BA,
- Sleeps 10
Serenity Abounds in Brand New Waterfront Florida Keys Getaway
- 3 Bedrooms, Sleeps 8
- 3 BR,
- Sleeps 8
Elegant Open Water, Boat Dock and Sandy Beach
- 4 Bedrooms,
- 3 Bathrooms, Sleeps 10
- 4 BR,
- 3 BA,
- Sleeps 10
3 Bedroom Island Home Surrounded by Warm Caribbean Water
- 3 Bedrooms, Sleeps 6
- 3 BR,
- Sleeps 6
Sweet Views with a Pool, Summer Months Available!!!
- 3 Bedrooms, Sleeps 6
- 3 BR,
- Sleeps 6
Beautiful Pool Home in Sugarloaf Key
- 3 Bedrooms,
- 2 Bathrooms, Sleeps 6
- 3 BR,
- 2 BA,
- Sleeps 6
Sugarloaf Paradise:Pool, Private on Canal/Fish/Swim/Boat Backyard
- 4 Bedrooms, Sleeps 10
- 4 BR,
- Sleeps 10
Bamboo Palms Open Water Home W/ Heated Pool/Hot Tub/Kayaks/Bikes
- 4 Bedrooms,
- 2 Bathrooms,
- 1 Half Bath, Sleeps 12
- 4 BR,
- 2 BA,
- 1 HF BA,
- Sleeps 12
Canal front ground level single family rental with dockage
- 3 Bedrooms,
- 3 Bathrooms,
- 1 Half Bath, Sleeps 6
- 3 BR,
- 3 BA,
- 1 HF BA,
- Sleeps 6
Beachfront Home on Sugar Sand Beach,Tropical,Private and Gated
- 2 Bedrooms, Sleeps 4
- 2 BR,
- Sleeps 4
Waterfront Paradise with Privacy and Sunshine
- 4 Bedrooms, Sleeps 8
- 4 BR,
- Sleeps 8
Keys Living at its Best
- 3 Bedrooms, Sleeps 8
- 3 BR,
- Sleeps 8
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